Sodium Hydroxide → 2-[2-(3,5-Dimethylphenyl)acetamido]-3-phenyl-propionic acid

HRID 71019Notes

Reaction equation

HRID 71019 reaction equation
[OH-].[Na+].[CH3:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([NH:14][CH:15]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:16]([O:18]C)=[O:17])=[O:13])[CH:7]=[C:8]([CH3:10])[CH:9]=1>>[CH3:3][C:4]1[CH:5]=[C:6]([CH2:11][C:12]([NH:14][CH:15]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:16]([OH:18])=[O:17])=[O:13])[CH:7]=[C:8]([CH3:10])[CH:9]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 67042062Methyl 2-[2-(3,5-dimethylphenyl)acetamido]-3-phenyl-propanoate

Product 1

HCID 670420812-[2-(3,5-Dimethylphenyl)acetamido]-3-phenyl-propionic acid

Procedure

A solution of NaOH 1N (7.8 ml, 7.83 mmol) was added to a methanolic solution (40 ml) of (S) methyl 2-[2-(3,5-dimethylphenyl)acetamido]-3-phenyl-propanoate (635 mg, 1.95 mmol) and the reaction mixture was stirred for 1 h at rt, then concentrated under reduced pressure and residue diluted with H2O (40 ml) and HCl 1N to obtain a pH value equal to 2. The crude organic product was extracted with ethyl acetate (3×40 ml) and the organic phase was dried with anhydrous Na2SO4. The solvent was removed under reduced pressure to afford (S) 2-[2-(3,5-dimethylphenyl)acetamido]-3-phenyl-propionic acid as white solid with nearly quantitative yield.

Workup

  1. concentrationconcentrated under reduced pressure and residue
  2. additiondiluted with H2O (40 ml) and HCl 1N
  3. customto obtain a pH value equal to 2
  4. extractionThe crude organic product was extracted with ethyl acetate (3×40 ml)
  5. dry with materialthe organic phase was dried with anhydrous Na2SO4
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-26630f8e27034f27bc1d4508f9f941d9
Source dataset
uspto-grants-2014_09
Patent number
US08822698B2

Reaction notes

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